O’Keeffe was first introduced to the Lake George area in 1907, when she was a student at the Art Students League and received a scholarship to paint in the region. Similar to other Lake George landscapes of the early to mid-1920s, My Shanty reveals a vocabulary of simplified forms, precise edges, and repeated horizontals. The old farm building, which served as the artist's summer studio, is solid and clearly defined. O'Keeffe's precise depiction of the shanty is offset by the diffuse rendering of pink and orange wildflowers and verdant trees and grass, as well as the curving sweep of the blue-toned hills and clouds overhead. Although it is seemingly a literal depiction of the building, the composition cannot be classified simply as representational or precisionist. It illustrates O'Keeffe's tendency to overlay objective fact with spiritual and symbolic meanings; at the end of the building's gable roof, the triangular shape of the structure is emphasized, a compositional choice that O’Keeffe may have derived from the theories of Wassily Kandinsky, who believed that the triangle was a symbol of the soul.

During this time, O’Keeffe’s paintings and Stieglitz’s photographs are comparable; both artists created works that can be read as symbolic self-portraits, reflecting their individual temperament as well as artistic intent. In My Shanty, O'Keeffe presents herself indirectly, alluding to a deeper, almost supernatural or mysterious level of understanding. The open doors to the structure make the viewer aware of the interior even as they deny access, and the white window frame and mullion become the focal point. The window becomes the painting’s core and as the only area of intense brightness, it may function as a symbol: as an eye to her soul, both revealed and obscured. Underscoring this interpretation is the importance of the color white to both O'Keeffe and Stieglitz. They shared a symbolist understanding of white and frequently invoked it—O'Keeffe in her art and Stieglitz in his writing and photography—to refer to ideas, events, and people.

My Shanty was one of three O'Keeffe works that Duncan Phillips had on approval in 1926, the other two oil paintings were returned to Stieglitz. Phillips was drawn to its "atmosphere of portentous solitude" and "stark expression of a somber Celtic mood," a characterization that O'Keeffe later discounted. As she recalled, she had painted My Shanty in response to the criticism of the men in Stieglitz's circle—Arthur Dove, John Marin, Charles Demuth, Marsden Hartley, and the photographer Paul Strand. In an effort to satisfy them, O’Keefe abandoned her vision of painting in clean and clear colors and adopted their dreary color scheme. Only after doing so did the men approve of her work and recognize her ability as painter.